Acetyl chloride → 1-acetoxy-7-cyano-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione

HRID 346144Notes

Reaction equation

HRID 346144 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([NH:7][C:8](=[O:15])[C:9](=[O:14])[N:10]2[OH:13])=[CH:5][C:4]=1[C:16]([F:19])([F:18])[F:17])#[N:2].C(N(CC)CC)C.[C:27](Cl)(=[O:29])[CH3:28]>O1CCCC1>[C:27]([O:13][N:10]1[C:11]2[C:6](=[CH:5][C:4]([C:16]([F:19])([F:17])[F:18])=[C:3]([C:1]#[N:2])[CH:12]=2)[NH:7][C:8](=[O:15])[C:9]1=[O:14])(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 199904677-cyano-1-hydroxy-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione

Product 1

HCID 199904121-acetoxy-7-cyano-6-trifluoromethylquinoxaline-2,3(1H,4H)-dioneYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.4 g (1.48 mmol) 7-cyano-1-hydroxy-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione in 50 ml dry tetrahydrofuran was added 0.3 ml (2.18 mmol) dry triethylamine and 0.15 ml (2.10 mmol) acetyl chloride. The mixture was refluxed for 3 h, and then evaporated in vacuo. The residue was stirred with water to give 0.42 g (92%) of 1-acetoxy-7-cyano-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione. M.p. 230° C. 1H-NMR (DMSO-d6): 8.16 (1H, s), 7.53 (1H, s), 2.37 (3H, s).

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-8ffd17ef78204d8e877df1910aa90bf3
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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